1. Technical Field
The present invention generally relates to trifluorovinyl aromatic containing poly(alkyl ether) prepolymers, e.g., poly(alkyl ether) prepolymers having terminal trifluorovinyl aromatic ether groups, and homo and copolymers produced from such prepolymers. The prepolymers and resulting polymers are useful as biomedical devices such as contact lenses or intraocular lenses.
2. Description of Related Art
In the field of biomedical devices such as contact lenses, various physical and chemical properties such as, for example, oxygen permeability, wettability, material strength and stability are but a few of the factors that must be carefully balanced in order to provide a useable contact lens. For example, since the cornea receives its oxygen supply exclusively from contact with the atmosphere, good oxygen permeability is a critical characteristic for any contact lens material. Wettability also is important in that, if the lens is not sufficiently wettable, it does not remain lubricated and therefore cannot be worn comfortably in the eye. Accordingly, the optimum contact lens would have at least both excellent oxygen permeability and excellent tear fluid wettability.
Contact lenses made from fluorinated materials have been investigated for a number of years. Such materials can generally be subdivided into two major classes, namely hydrogels and non-hydrogels. Hydrogels can absorb and retain water in an equilibrium state whereas non-hydrogels do not absorb appreciable amounts of water. Regardless of their water content, both hydrogel and non-hydrogel fluorinated contact lenses tend to have relatively hydrophobic, non-wettable surfaces.
By introducing fluorine-containing groups into contact lens polymers, the oxygen permeability can be significantly increased. For example, U.S. Pat. No. 4,996,275 discloses using a mixture of comonomers including the fluorinated compound bis(1,1,1,3,3,3-hexafluoro-2-propyl)itaconate in combination with organosiloxane components. Fluorinating certain polysiloxane materials has been indicated to reduce the accumulation of deposits on contact lenses made from such materials. See, for example, U.S. Pat. Nos. 4,440,918; 4,954,587; 4,990,582; 5,010,141 and 5,079,319. However, fluorinated polymers can suffer from one or more of the following drawbacks: difficult and/or expensive synthetic routes, poor processability, low refractive index, poor wettability, poor optical clarity, poor miscibility with other monomers/reagents and toxicity.
The thermal polymerization products of trifluorovinyl-containing monomers, e.g., bis-trifluorovinyl monomers, to form perfluorocyclobutylene polymers are known. See, e.g., U.S. Pat. Nos. 5,021,602; 5,023,380; 5,037,917; 5,037,918; 5,037,919; 5,066,746; 5,159,036; 5,159,037; 5,159,038, 5,162,468; 5,198,513; 5,210,265; 5,246,782; 5,364,547; 5,364,917 and 5,409,777. U.S. Pat. No. 5,225,515 discloses poly(aromatic ether) polymers or copolymers containing perfluorocyclobutane rings in the polymer backbone. U.S. Pat. Nos. 5,246,782 and 5,409,777 further disclose that the polymers are useful as, for example, passivation coatings on medical instruments and in packaging for medical devices such as bandages and operating equipment. However, there has been no recognition or appreciation of trifluorovinyl aromatic containing poly(alkyl ether) prepolymers or that such prepolymers can be employed in the manufacture of biomedical devices and particularly contact lens applications.
Accordingly, it would be desirable to provide improved fluorinated materials for use in the manufacturing of biomedical devices for prolonged contact with the body while also being biocompatible.